98775-10-1

Upstream product

• 65143-37-5 2-oxo-2-(4-tolyl)ethyl acetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 70964-89-5 E-methyl β-methyl-p-methylcinnamate 
• 103675-24-7 (Z)-4-(Tetrahydro-pyran-2-yloxy)-3-p-tolyl-but-2-enoic acid methyl ester 
• 201230-82-2 carbon monoxide 
• 766-97-2 4-n-methylphenylacetylene 
• 89359-17-1 β-(4-methylphenyl)-γ-butyrolactone 
• 471931-08-5 4-(p-toluenesulfonyloxy)-2(5H)-furanone 
• 624-31-7 4-tolyl iodide 
• 94853-53-9 ethyl 3-(4-methylphenyl)-2-butenoate 
• 4508-99-0 methyl γ-hydroxycrotonate 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 1174747-81-9 C₁₅H₂₁O₆P 
• 1289389-84-9 (E)-3,4-diiodobut-2-enoic acid 

Downstream Products

• 185342-38-5 5-Bromo-4-p-tolyl-5H-furan-2-one 
• 20842-10-8 3-(4-methylphenyl)furan 
• 185342-43-2 5-Methoxy-4-p-tolyl-5H-furan-2-one 

Relevant academic research and scientific papers

Gold-catalyzed cascade oxidative cyclization and arylation of allenoates

An AuI/AuIII catalytic system was found to be effective for the cascade oxidative arylation and cyclization of allenoates with arylboronic acids to give the corresponding cyclic adducts in moderate yields. This reaction system constitutes a new method for the synthesis of β-aryl-γ-butenolides under mild conditions. Based on the previous mechanistic studies, a proposed AuI/AuIII redox catalytic cycle has been outlined. An AuI/AuIII catalytic system was found to be effective for the cascade oxidative arylation and cyclization of allenoates with various arylboronic acids to give the corresponding cyclic adducts in moderate yields. This reaction system enabled the synthesis β-aryl-γ-butenolides under mild conditions. Based on previous mechanistic studies, an AuI/AuIII redox catalytic cycle has been outlined. Copyright

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf) 2, which is in situ prepared from PhI(OAc) 2 and Me 3 SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5 H)-ones or furan-2(3 H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.

Hg/Pt-catalyzed conversion of bromo alkynamines/alkynols to saturated and unsaturated γ-butyrolactams/lactones via intramolecular electrophilic cyclization

Convenient and general Hg(ii)/Pt(iv) catalyzed syntheses of γ-butyrolactams and α,β-unsaturated γ-butyrolactones/lactams are described via intramolecular electrophilic cyclizations of bromoalkynes with tosylamino and hydroxyl tethers. The reaction features the use of wet solvents, the exclusion of any base and additive, mild conditions and practical yields. We also synthesised few chiral lactams through this pathway. Additionally, it is shown that the NHTs group distanced further from the homopropargylic position assists regioselective bromoalkyne hydration to yield useful α-bromoketones. Furthermore, Boc protected bromo homo propargyl amines undergo 6-endo-dig cyclization through Boc oxygen to give bromomethylene substituted oxazinones.

Rapid access to 4-substituted-pyrones and 2(5H)-furanones via a palladium-catalyzed C-OH bond activation

An efficient palladium-catalyzed cross-coupling reaction of 4-hydroxy-pyrone or 4-hydroxy-2(5H)-furanone with arylboronic acid is described, which affords the 4-substituted-pyrones and 2(5H)-furanones in good yields. This transformation proceeds through a C-OH bond activation under mild conditions.

Synthesis and reactivity of β,γ-dihalogenated unsaturated acids: Application to the synthesis of 4-substituted 5 H -furan-2-ones

β,γ-Dihalogenated unsaturated acids were prepared regio- and stereoselectively from allenic acid, and some aspects of their reactivities were studied. Georg Thieme Verlag Stuttgart · New York.

Novel and efficient route for the synthesis of 4-Aryl-substituted 2(5H)-furanones

4-Aryl-substituted 2(5H)-furanones were prepared by reaction of diethylphosphono acetic acid and phenacyl bromides, followed by an intramolecular Horner-Emmons-type cyclization. Both the reactions were carried out in situ to give the desired 4-aryl substituted 2(5H)-furanone derivatives.

Palladium-catalyzed reaction of arenediazonium tetrafluoroborates with methyl 4-hydroxy-2-butenoate: An approach to 4-aryl butenolides and an expeditious synthesis of rubrolide E

The palladium-catalyzed reaction of arenediazonium tetrafluoroborates with methyl 4-hydroxy-2-butenoate in MeOH under mild conditions gives 4-arylbutenolides usually in good to high yields through a domino vinylic substitution/cyclization process. The rea

Rh(I)-catalyzed cross-coupling reactions of alkenyl tosylates with potassium aryltrifluoroborates

RhCl(PPh3)3/DPPF was successfully employed as an efficient catalyst in the Suzuki-Miyaura cross-coupling reactions of potassium aryltrifluoroborates with alkenyl tosylates, affording the corresponding products in good to excellent yi

An expedient palladium-mediated route to 3-arylfurans

A facile route to 3-arylfurans has been developed by employing the Heck reaction between 2,5-dihydro-2,5-dimethoxyfuran and aryl iodides as the key step.

An expeditious synthesis of 4-aryl-γ-butyrolactones, -furan-2(5H)-ones and -5-alkoxyfuran-2(5H)-ones via Heck-reaction of arenediazonium salts with 2,5-dihydrofuran

An exceptionally simple and short synthetic sequence to 4-substituted furan-2(5H)-ones involving a Heck reaction on 2,5-dihydrofuran and subsequent iterative NBS oxidation is described.